In the whirlwind world of baseball deals and drama, Day 2 of the MLB Winter Meetings exploded with big moves that could reshape teams for the 2026 season—get ready to dive into the action that had fans buzzing! But here's where it gets controversial: Are agents like Scott Boras just clever entertainers, or are they manipulating the market with their cryptic clues? Stick around to see how these signings and hints might stir up debates about fairness in free agency.
The Athletic is providing live updates on the 2025 MLB Winter Meetings right here: (https://www.nytimes.com/athletic/live-blogs/mlb-winter-meetings-live-updates/SlFTbV0agdkE/).
ORLANDO, Fla. — While Day 1 felt a bit sluggish, Day 2 ramped up the intensity with a flurry of announcements squeezed into a short midday window. Right around noon, two high-profile free agents locked in lucrative deals, coinciding with the sport's most influential agent captivating the press with his enigmatic remarks. This is pretty typical for the Winter Meetings, where surprises often unfold in bursts.
The final day of this year's gatherings wraps up on Wednesday. To ensure you're fully caught up, let's break down the major developments from Day 2, starting with the blockbuster signings that shifted the offseason landscape.
The standout deal of the week so far
After a lull in activity for the top free agents, Tuesday morning brought a wave of excitement when Kyle Schwarber, ranked as the No. 4 free agent on MLB's Big Board—a handy ranking system that evaluates players based on their talent, age, and market value—inked a five-year, $150-million contract with the Philadelphia Phillies.
This move wasn't shocking at all; Schwarber was simply returning to a team he'd joined in 2022, and the terms matched almost exactly what The Athletic had forecasted over a month ago (https://www.nytimes.com/athletic/6774254/2025/11/04/mlb-free-agent-contract-projections/). Still, it marked the first major offensive boost in an offseason that's been dominated by pitching acquisitions. For instance, think of it as adding a powerful slugger who can drive in runs and energize the lineup, much like how a star quarterback can turn around a football team's fortunes. This signing also provided clarity for the Phillies, a squad still in their prime competitive phase but navigating significant player turnover to stay contenders.
Moreover, Schwarber's agreement might ease some congestion in the free agent pool, particularly for positions like first base or designated hitter—roles that require versatile hitters who can handle the bat without needing to play a defensive position every day.
The Dodgers snag another elite reliever
Almost simultaneously with the Schwarber news, The Athletic's Will Sammon revealed that top free agent closer Edwin Díaz had agreed to a three-year, $69-million pact with the Los Angeles Dodgers (https://www.nytimes.com/athletic/6837757/2025/12/09/mlb-edwin-diaz-free-agency-signing-dodgers/). This follows their signing of Tanner Scott last year, making it two winters in a row they've landed the Big Board's top-ranked reliever.
Díaz, now 31, has been a Mets stalwart since 2019, cementing his reputation as one of the most dependable closers in the game. Last season was a comeback story for him, earning his third All-Star nod and topping NL relievers in Win Probability Added—a statistic that measures how much a player's performance increases their team's chances of winning a game. Imagine a pitcher who consistently shuts down opponents in high-pressure situations, like a goalkeeper sealing a soccer match.
In Los Angeles, Díaz is expected to step into the closer role, replacing Tanner Scott, who faced challenges there last year. At an average of $23 million per season, this contract sets a new record for the highest annual value ever paid to a relief pitcher, underscoring the Dodgers' commitment to elite bullpen talent.
Boras takes the spotlight with clever riddles
As is tradition during the Winter Meetings, agent Scott Boras hosts a media gathering where he responds to inquiries using a mix of puns, analogies, and humorous quips.
On Tuesday, his responses included veiled hints about Cody Bellinger's negotiations, which, if deciphered correctly, point to interest from teams like the Yankees, Reds, Mets, Dodgers, Phillies, Giants, Blue Jays, and Angels (https://www.nytimes.com/athletic/6876011/2025/12/09/cody-bellinger-yankees-scott-boras/). Here's what he quipped:
“It’s not for me to judge, but great players see red if they have a big bat yanked out of their lineup. I haven’t met a team that dodges a five-tool player. To fill the center-field need is a giant step towards the playoffs. North and South outfielders that fly with power, they’re rare birds. In the offseason, there’s a lot of startup to organizations, and for that reason, there’s a lot of angel investors that are looking for very versatile outfielders. So, other than that, Belli doesn’t have much interest.”
And this is the part most people miss: Is Boras' coded language a harmless bit of fun, or does it give some teams an unfair edge in negotiations? It certainly sparks debate about transparency in the sport.
Boras also made an appearance at MLB's main event, part of the announcement for Toronto Blue Jay Dylan Cease's seven-year, $210-million deal, which was finalized last week.
Could the Diamondbacks be gearing up for a Marte swap?
Ken Rosenthal reported on Tuesday that the Arizona Diamondbacks are entertaining discussions about trading second baseman Ketel Marte (https://www.nytimes.com/athletic/6874837/2025/12/09/mlb-trade-market-winter-meetings-ketel-marte/), and even if no deal happens this week, these talks could pave the way for a future agreement.
Marte, 32, is under contract for six more years at $102.5 million—a steal for one of baseball's premier middle infielders. Rosenthal notes the Diamondbacks are aiming for a blockbuster return, but teams must be prepared to shoulder any potential clubhouse issues that arose in Arizona. For beginners, this means evaluating not just a player's stats but also how they fit team chemistry, like adding a talented but moody artist to a band.
Potential suitors include the Boston Red Sox, who are actively seeking offensive upgrades. They're pursuing free agents like Alex Bregman, Bo Bichette, and Pete Alonso, while also eyeing trade targets such as Marte and Houston Astros third baseman Isaac Paredes.
Mets might offer up star pitcher Peterson
In their quest for more hitting power, the New York Mets are open to dealing reliable starter David Peterson, as reported by Tim Britton and Will Sammon on Tuesday (https://www.nytimes.com/athletic/6875757/2025/12/09/mets-david-peterson-trade-market/). Peterson, an All-Star, is in his final season of team control and led the Mets with 168 2/3 innings pitched last year.
The Mets are leaning toward a straight-up trade, similar to last year's swap of outfielder Brandon Nimmo for second baseman Marcus Semien. They have gaps to fill at first base, designated hitter, outfield, and bullpen—positions crucial for scoring runs and securing wins.
Orioles ready to open their wallets
Under new ownership, brimming with young prospects, and desperately needing starting pitchers, the Baltimore Orioles are an intriguing wildcard this offseason. Recent reports indicate they're prepared to invest heavily in top free agents. Rosenthal revealed they matched the Phillies' $150-million bid for Schwarber (https://www.nytimes.com/athletic/6876322/2025/12/09/kyle-schwarber-orioles-phillies-mlb-free-agency/). They've also engaged in conversations for nearly every elite free agent except infielders Alex Bregman and Bo Bichette, who don't align with Baltimore's needs.
Team USA bolsters its roster
Tuesday unofficially became World Baseball Classic Day at the Meetings, with Team USA announcing additions of Schwarber, Gunnar Henderson, Will Smith, and Brice Turang to their squad (https://www.nytimes.com/athletic/6875699/2025/12/09/kyle-schwarber-usa-2026-world-baseball-classic/), joining stars like Aaron Judge, Paul Skenes, Cal Raleigh, Bobby Witt Jr., Corbin Carroll, and Pete Crow-Armstrong.
Other WBC buzz included Cuban reliever Aroldis Chapman possibly suiting up for Great Britain (https://www.nytimes.com/athletic/6876292/2025/12/09/boston-red-sox-aroldis-chapman-team-great-britain-wbc/)—thanks to his Jamaican heritage, as Jamaica was a British colony until 1962. Meanwhile, Team Venezuela stood up for their nation and people (https://www.nytimes.com/athletic/6876607/2025/12/09/venezuela-wbc-manager-omar-lopez-trump-visas/) in response to criticisms and visa threats from President Trump.
White Sox strike gold in the draft lottery
The Chicago White Sox clinched Tuesday's draft lottery, securing the No. 1 pick for next summer's draft. They'll be followed by the Tampa Bay Rays and Minnesota Twins. The Colorado Rockies, despite their dismal 2025 record, were ineligible after recent lottery wins and will pick 10th.
Red Sox and Angels execute a small trade
In a minor but noteworthy exchange, the Boston Red Sox traded infielder Vaughn Grissom to the Los Angeles Angels in return for 21-year-old outfield prospect Isaiah Jackson. Grissom was the key piece acquired in the 2023 deal sending Chris Sale to the Atlanta Braves. Since then, he's battled injuries and inconsistent play, spending the entire 2025 season in Triple-A with a .783 OPS while covering all infield spots. At just 24, he's shown flashes of potential as a versatile, offense-focused middle infielder across parts of three MLB seasons.
Phillies lock in manager Thomson
Building on Day 1's news of nearing a bench coach deal with Don Mattingly, the Phillies on Day 2 confirmed an extension for manager Rob Thomson (https://www.nytimes.com/athletic/6875892/2025/12/09/rob-thomson-phillies-contract-extension-2027/) through the 2027 season. Thomson, who stepped in as interim manager in 2022 and led them to the World Series, has reached the playoffs every year in his role, including consecutive division titles.
Baldelli steps into the Dodgers' front office
Ex-Minnesota Twins manager and Tampa Bay Rays outfielder Rocco Baldelli has joined the Los Angeles Dodgers as a special assistant (https://www.nytimes.com/athletic/6876286/2025/12/09/dodgers-rocco-baldelli-twins-front-office/). He shares a deep history with Dodgers president Andrew Friedman, who was once the Rays' GM.
As we wrap up this recap, here's a controversial angle to ponder: With teams like the Dodgers and Phillies splashing cash, are we seeing a widening gap between haves and have-nots in baseball, potentially hurting competitive balance? And what about those coded agent hints—do they level the playing field or just add to the chaos? Share your thoughts in the comments: Do you agree that big spenders should face salary caps, or is this free-market frenzy what makes the sport exciting? Let's hear your takes!
